Abstract
Heterotrophic cell suspension cultures of soya (Glycine max) and photomixotrophic cell suspension cultures of rape (Brassica napus) were incubated with cis-9-[1-14C]octadecenol for 3–48 h. It was found that under aerobic conditions large proportions of the alcohol are oxidized to oleic acid, which is incorporated predominantly into phospholipids, whereas up to 30% of the substrate is esterified to wax esters. This is true for both the heterotrophic and the photomixotrophic cell suspension cultures, but the metabolic rates are much higher in the latter. Under anaerobic conditions only small proportions of the radioactively labeled alcohol are oxidized to oleic acid, whereas a major portion of the alcohol is esterified to wax esters both in heterotrophic and photomixotrophic cultures. Incubations of homogenates of photomixotrophic rape cells with labeled cis-9-octadecenol showed that pH 6 is optimum for the formation of wax esters. This monounsaturated alcohol is preferred as a substrate over saturated longchain alcohols, whereas short-chain alcohols, cholesterol, and glycerol are not acylated. Incubations of an enzyme concentrate from a homogenate of rape cells with unlabeled cis-9-octadecenol and [1-14C]oleic acid, or [1-14C]stearoyl-CoA, or di[1-14C]palmitoyl-sn-glycero-3-phosphocholine showed that acylation of the longchain alcohol proceeds predominantly through acyl-CoA. Direct esterification of the alcohol with fatty acid as well as acyl transfer from diacylglycerophosphocholine could be demonstrated to occur to a much smaller extent.
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References
Brown, W.G. (1951) Reductions by lithium aluminium hydride. Org. React. 6, 469–509
Chalvardjian, A. (1964) Fatty acids of brown and yellow fat in rats. Biochem. J. 90, 518–521
Gamborg, O.L., Miller, R.A., Ojima, K. (1968) Nutrient requirements of suspension cultures of soybean root cells. Exp. Cell Res. 50, 151–158
Gamborg, O.L., Shyluck, J.P. (1970) The culture of plant cells with ammonium salts as the sole nitrogen source. Plant Physiol. 45, 598–600
Kates, M. (1970) Plant phospholipids and glycolipids. Adv. Lipid Res 8, 225–265
Kates, M., Eberhardt, F.M. (1957) Isolation and fractionation of leaf phosphatides. Can. J. Bot. 35, 895–905
Kaufmann, H.P., Mangold, H.K., Mukherjee, K.D. (1971) Chromatography of unusual lipids on thin layers of magnesium oxide. J. Lipid Res. 12, 506–509
Kolattukudy, P.E. (1967) Mechanisms of synthesis of waxy esters in broccoli (Brassica oleracea). Biochemistry 6, 2705–2717
Kolattukudy, P.E. (1975) Biochemistry of cutin, suberin and waxes, the lipid barriers on plants. In: Recent advances in the chemistry and biochemistry of plant lipids, pp. 203–246, Galliard, T., Mercer, E.I., eds. Academic Press, New York London
Kolattukudy, P.E. (1976) Introduction to natural waxes. In: Chemistry and biochemistry of natural waxes, pp. 1–15, Kolattukudy, P.E., ed. Elsevier, Amsterdam New York
Mahadevan, V. (1970) Chemistry and metabolism of fatty aldehydes. Progr. Fats Other Lipids 11, 83–135
Mahadevan, V. (1978) Fatty alcohols: chemistry and metabolism. Progr. Fats Other Lipids 15, 255–299
Mangold, H.K. (1972) The search for alkoxylipids in plants. In: Ether lipids, pp. 399–405, Snyder, F., ed. Academic Press, New York London
Mangold, H.K. (1979) Synthesis and biosynthesis of alkoxylipids. Angew. Chem. Int. Ed. Engl. 18, 493–503
Mangold, H.K., Becker, H., Cramer, U., Spener, F. (1976) Homologous synthesis: a method for the preparation of mixed substrates and individual compounds. Chem. Phys. Lipids. 17, 176–181
Mangold, H.K., Malins, D.C. (1960) Fractionation of fats, oils, and waxes on thin layers of silicic acid. J. Am. Oil Chem. Soc. 37, 383–385
Moreau, R.A., Huang, A.H.C. (1977) Gluconeogenesis from storage wax in the cotyledons of jojoba seedlings. Plant Physiol. 60, 329–333
Murashige, T., Skoog, F. (1962) A revised medium for rapid growth and bioassay with tobacco cultures. Physiol. Plant. 15, 473–479
Radwan, S.S., Mangold, H.K. (1979) Biochemistry of lipids in plant cell cultures. In: Advances in biochemical engineering, vol. 16, pp. 109–133, Fiechter, A., ed. Springer, Berlin Heidelberg New York
Richter, I., Mukherjee, K.D., Weber, N. (1981) Biosynthesis of wax esters in tissues of Sinapis alba L. seeds. Planta 151, 381–384
Richter, I., Weber, N., Mangold, H.K., Mukherjee, K.D. (1978) Incorporation of positional isomers of cis- and trans-octadecenoic-acids into the acyl lipids of cultured soya cells. Z. Naturforsch. 33c, 303–304
Robinson, H.W., Hogden, C.G. (1940) The biuret reaction in the determination of serum proteins. I. A study of the conditions necessary for the production of a stable color which bears a quantitative relationship to the protein concentration. J. Biol. Chem. 135, 707–726
Stumpf, P.K., Weber, N. (1977) Uptake and metabolism of fatty acids by soybean suspension cells. Lipids 12, 120–124
Wagner, H., Hörhammer, L., Wolff, P. (1961) Dunnschicht-chromatographie von Phosphatiden und Glykolipiden. Biochem. Z. 334, 175–184
Weber, N. (1978) Metabolism of cholesterol in cell suspension cultures of rape and soya. Z. Pflanzenphysiol 87, 355–363
Weber, N., Richter, I., Mangold, H.K., Mukherjee, K.D. (1979) Positional specificity in the incorporation of isomeric cisand trans-octadecenoic acids into glycerolipids of cultured soya cells. Planta 145, 479–485
Wu, X.-Y., Moreau, R.A., Stumpf, P.K. (1981) Studies of biosynthesis of waxes by developing jojoba seed. III. Biosynthesis of wax esters from acyl-CoA and long-chain alcohols. Lipids 16, 897–902
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Weber, N., Mangold, H.K. Metabolism of long-chain alcohols in cell suspension cultures of soya and rape. Planta 155, 225–230 (1982). https://doi.org/10.1007/BF00392720
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DOI: https://doi.org/10.1007/BF00392720